Lithium Hydroxide → HCID 86751796, compound

HRID 1941560Notes

Reaction equation

HRID 1941560 reaction equation
[NH2:1][N:2]=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:35])[CH2:12][CH2:13][C:14]([NH:16][CH2:17][CH:18]([C:24]2[C:29]([F:30])=[C:28]([F:31])[C:27]([F:32])=[C:26]([F:33])[C:25]=2[F:34])[C:19]([O:21]CC)=[O:20])=[O:15])=[CH:6][CH:5]=1.[OH-].[Li+].C(O)(C(F)(F)F)=O>O.C(#N)C>[NH2:1][N:2]=[CH:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:35])[CH2:12][CH2:13][C:14]([NH:16][CH2:17][CH:18]([C:24]2[C:25]([F:34])=[C:26]([F:33])[C:27]([F:32])=[C:28]([F:31])[C:29]=2[F:30])[C:19]([OH:21])=[O:20])=[O:15])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 86751797HCID 86751797, compound

Product 1

HCID 86751796HCID 86751796, compoundYield 109.5%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Ethyl β[[4-[[4-(aminoiminomethyl)phenyl]-amino]-1,4-dioxobutyl]amino]-(pentafluorophenyl)propanoate prepared in Example 59 (600 mg) was added to water/acetonitrile (20 ml) followed by lithium hydroxide (100 mg) at 25° C. The mixture was stirred for 30 min. The course of the reaction was monitored by RPHPLC. After satisfactory acid was formed the reaction was neutralized with TFA and purified by reverse phase chromatography (water/acetonitrile) to result in 620 mg of a white solid: 1H NMR (d6 -DMSO) δ2.38 (t, 2H, J=7.3 Hz), 2.44 (d, 2H, J=6.4 Hz), 2.56 (t, 2H, J=7.3 Hz), 4.32 (m, 1H), 7.78 (s, 4H), 7.99 (d, 1H,J=8.1 Hz), 8.92 (bs, 2H), 9.16 (bs, 2H), 10.39 (s, 1H); MS (FAB) m/z 365.2 (MH+).

Workup

  1. customAfter satisfactory acid was formed the reaction
  2. custompurified by reverse phase chromatography (water/acetonitrile)

Sources & evidence

ORD record
ord-f2777b18bec34d0583cf1fcd66756ad9
Source dataset
uspto-grants-1997_12
Patent number
US05703125

Reaction notes

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